Cuba conjures up images of classic cars, mojitos and salsa music, but for so long, the island – the largest in the Carribbean – has been somewhat of a question mark for travellers.
For decades, it was a mystery. Tourism all but stopped after the revolution in 1959, only to start again in the early 90s, after the collapse of the Soviet Union.
It was only eight years ago, that President Obama lifted the travel ban for Americans, marking a new era for tourism on the island.
Today, the country still raises eyebrows. ‘Is Cuba safe?’, my friends asked as I detailed my planned adventure across the country for two weeks. ‘I’m sure it’ll be fine,’ I had hastily replied.
Talk about an understatement. I was so captivated by the place that I intentionally missed my flight back to London, and stayed an extra week in paradise.
And don’t just take my word for it: Cuba has just been named by Condé Nast Traveller in their list of the best 25 places to go in 2025 with the publication citing its ‘UNESCO-protected cities, gelato-colored classic cars — and its loquacious, quick-witted locals’ as reasons to visit.’
I began my journey in Havana, touching down in the capital in late February 2024.
I had signed up for a group trip experience with WeRoad, who had planned five stops on our itinerary including villages and cities that would showcase all that Cuba had to offer.
So, if you’re planning a road trip with a difference, here’s how to spend three weeks in Cuba.
WeRoad's Cuba 360°: from Havana to Trinidad
This 12-day small group adventure tour around Cuba is priced from £1,049 per person to include 11 nights’ accommodation on bed and breakfast basis, a welcome dinner, transport in Cuba, excursions and experiences, including a horse ride among the tobacco plantations in Viñales, catamaran (or boat depending on availability) excursion to Cayo Iguana, walking tour of Old Havana with local guide, guided 2-hour vintage car ride in Havana and services of a travel coordinator. To book visit the We Road website.
Flights were not included, but you can get good deals if you’re willing to take a flight with a layover. My flight were £920 return from London Gatwick, with a stop in Madrid.
Havana (4/5 days)
Cuba’s capital is beautiful. The city is unlike anything I have ever seen before: the marvel of the renaissance-esque buildings that were crumbling away, the hustle and bustle of the streets and the incredible culture.
You’ve likely seen pictures of the classic cars driving past sun bleached buildings – actually being there was like seeing a postcard come to life.
We stayed in homestays, which are private homes that local families rent out to tourists, for around $30 a night, with discounts available if you stay longer.
The hosts were incredibly welcoming, and it’s a lot more affordable than staying in one of the hotels. Some will even make you breakfast (I enjoyed fruits and pastries), wash laundry for you, and help you organise activities.
I was also a similar age to some of the people working in the homestays, who were all eager for me to look around the city.
While in Havana, be sure to do a classic car tour – you can see the whole city in style with a private driver. We booked with Old Cars Havana, who offer a trip in a classic convertible for $80 dollars, with an informative guide.
For nightlife and to immerse yourself in local culture, Fabrica de Art Cubano is the place to be. It will be the place recommended to you by tourists and locals alike.
Havana Checklist
- Zapata National Park to spot the vultures
- Lunch at ‘El Dandy’
- Go on a classic car tour
- Spend the night at Fabrica
- Do a Salsa class
- Dinner at Antojos
- Have a mojito at a bar along The Almendares River
The venue is an art gallery come music venue, with multiple rooms showing different performances. When I say I loved it, I mean it – I went three times. I saw a live band, DJ set, and salsa dancers. And, the best bit? The ticket was 600 pesos, which is around £3.
When it comes to food, Cuba isn’t exactly famed for its culinary delights. Due to trade embargos and tensions with the US, imports are scarce, meaning some of the meals you get won’t be the best.
That being said, Havana has the best food on the island. There were lots of fish-based dishes – although you can actually get sick of lobster if you eat it every day.
It is worth noting that everything in Havana was slightly more expensive than the other towns – with meals costing around £7-9, cocktails £4 and local beers about £1.50.
Solo Havana
The history degree sitting on my wall means that I am a certified museum enjoyer – and Havana is the perfect place to exercise this.
I dedicated a day to noseying around and visited the Museo Nacional de Bellas Artes, which houses traditional Cuban art in a classic Spanish colonial building, and the Museo de la Revolución, a former presidential palace which documents the history of Cuba from indigenous times to present day.
I then took myself for lunch at El Dandy on Plaza de Cristo, which became my favourite restaurant on the island, the staff took great interest in my name being Lucia (a popular Cuban name, despite my Cypriot heritage) and sat and chatted with me while I read my books.
Cubans are famous for their kind nature and hospitality, so there will always be a friendly face around to help if you need advice or recommendations.
Having loved my time in Havana so much, I wanted a unique souvenir to commemorate my trip, and what better way to do it than with some fresh ink?
I researched the highest rated tattoo parlour on TripAdvisor and was told that La Marca was the one.
As soon as I entered I knew I was about to get a good tat – the walls were filled with art decor, in traditional Cuban style.
I sat in the waiting room, flipping through the artists’ sketchbooks before I decided on an interpretation of a classic compass, which I thought was a nice nod to my travels.
The tattoo set me back $70, which, although may seem like a lot, was half what I would have paid in London, and I wanted to make sure I went to a reputable place.
Now, I look at my tattoo and think of the unforgettable trip.
Viñales (3/4 days)
I am not exaggerating when I say Viñales is the most beautiful place I have ever been in my life.
A three hour drive from Havana and in the valley region of the island, it is where most of the tobacco on the island comes from for those infamous cigars!
We spent three days here but I would recommend a little longer to take in the beauty of the incredible little town.
While in Viñales, we rode horseback across the mountains (which is much scarier than I remember horse-riding lessons being as a child), visited a tobacco plantation, and got up a 5am for a sunrise hike.
The tobacco plantation was a highlight, with the farmers giving us an in-depth tutorial on how to roll a cigar.
Once the leaves are picked, they are cured in special sheds for around two years before they are ready to be rolled.
I spent $70 on 12 cigars to bring home, which are now lying in my bedroom drawer, eagerly awaiting a special occasion. Our guide advised us to make sure we bought the cigars from verified tobacco plantations, as those on the streets are often fake.
Matanzas (2/3 days)
The port city of Matanzas, founded in 1693 by Spanish king Charles II, is rich in history and art.
It was a five hour drive from Viñales, but the spectacular views of rolling hills and mountainous regions made the journey fly past.
It is the nation’s second largest city, and has earned the nickname the ‘Athens of Cuba’ due to its cultural significance on the island.
Matanzas is overflowing with sculptures, and while walking through the city’s streets we spotted a man in his studio, making his head (not to scale) out of clay.
He proudly told us that he hadn’t been paid to make the artwork, which would be displayed in the town square, but he’s simply created it so there was more art available for locals.
While in Matanzas we also visited Cuevas de Bellamar, one of Cuba’s natural treasures.
The cave dates back 300,000 years, and our tour guide was quick to tell us the tales that have come into fruition over the years – including the ‘fountain of youth’ that flows through the rock formation.
Trinidad (3/4 days)
It’s hard to crown a champion, but Trinidad may be the best destination in Cuba. It’s on the south side of the island, so it has spectacular white sand beaches that have to be seen to be believed.
The town feels like Havana’s edgy younger sister – the Camden of the island, if you will.
We started off our stay with a dinner at a rooftop restaurant Muñoz Tapas, near the main square, which gave us an eagle eyed view of the bustling scenes below – there is always something going on in Cuba, be it a live performance, people dancing in the streets, or children running through the streets.
Dinner in Trinidad was around £6-8 for a meal, and drinks were £3 for a cocktail and £1 for local beers. I opted for some traditional croquetas with a pork and vegetable taco.
While in Trinidad, we frequented at Casa de la Musica, an open air music venue with a live band every night.In Cuba, people DANCE. None of this two step business that has plagued the clubs of London, but electric salsa moves and passionate rhythm.
If you don’t have a partner, no fear, if you look confused on the edge of the dance floor for more than twenty seconds, someone will be right over to sweep you off your feet.
After a few too many Mojitos at the Casa, head over to La Cueva.
About 200m below ground, ‘Gasolina’ and ‘Despacito’ can be heard vibrating through the walls of an actual underground cave, that’s now a nightclub.
The club somewhat resembles the nightclubs of Western Europe – sweaty and loud, but everyone is having a good time.
Our days in Trinidad looked very different to our hedonistic nights – hikes, ziplines and swimming in freshwater pools.
Head to El Cubano natural park where you can hike for hours, stopping off at a farmer’s house on the way for a cup of tea with leaves he’d grown himself, as part of the trek.
The trek wasn’t too demanding, however we were informed afterwards that we had taken the easier route, so if you want a challenge, you can opt for the harder one.
When we got to the top, rather than hiking back down, we paid $10 to zoom through the glorious treetops on a zipline, which was by far the most efficient way to descend.
Despite the dry climate when we visited, the biodiversity of the miniature rainforest was flourishing, and we even managed to catch a glimpse of Cuba’s national bird, the Tocroro, which sports the colours of the flag.
And, we couldn’t leave Trinidad without jumping on a boat and heading over to Cayo Blanco, an isle overrun by iguanas.
The huge reptiles seemed friendly enough, but I’d stay away from those jaws if you can.
Santa Clara (1 day)
Santa Clara pays homage to perhaps the most famous figure that comes to mind when thinking of Cuba, Ché Guevara.
It’s a poignant location in Guevara’s history as it was the site of one of the most pivotal battles during the revolution in 1958, where Che and his fighters derailed an armored train carrying troops and supplies for the President Batista’s regime, eventually leading to his resignation.
The central Cuban city has immortalised the battle, with the train proudly on display for visitors and locals alike.
Santa Clara was noticeably much less ‘busy’ than the other regions we had visited in Cuba. There was no music, few bars, and a cloud of defeat seemed to hang over the town, as the locals remembered those who had fought for their freedoms.
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We walked through the historic cobblestones with hushed voices, as a local guide told us of how the 1950s were the last marker of true revolution the country had seen.
Varadero (1/2 days)
Varadero is where you go if you’re looking for that typical Caribbean beach scene. It’s incredibly serene, but much more of a touristy location – for those looking to experience the ‘real’ Cuba, the other cities are worth the visit.
Aside from the white sands, you could very much be anywhere, and it lacked the heart and soul of the island that we had felt for the rest of the trip – the souvenir shops were full of classic ‘tat’ rather than the intrinsic art pieces and sculptures we had seen being created by local artists across the island.
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If you want to flop after a busy road-trip, this is the place, but if you don’t have much time to spare, I would give it a miss.
Top tips for travelling to Cuba
While beautiful, heading to Cuba can be quite an undertaking, and there are some logistical things worth noting when planning your trip.
- Blackouts. There are regular blackouts in the country, where there is either no water, no electricity, or both. This also means no WiFi or phone connection, so be prepared to spend time offline.
- Shops/Essentials. A lot of items that we deem to be essential are scarce in Cuba. Bring any medication you may need (including paracetamol and diarrhea tablets, for the weak bowelled readers), sanitary products, and hand sanitiser
- Snacks. If you need a sweet treat to get yourself through the day, bring some treats with you. I packed breakfast bars and some packets of crisps, as shops are few and far between.
- Phones To use your phone in Cuba (from the UK) you can pick up a sim card at the airport. Mine was around $12, and had enough data for three weeks
- Homestays. It’s easiest to book these on Airbnb, if you do it in advance, or if you’re looking for a last minute stay there will be places available – but be sure to rely on trusted recommendations.
- Spanish. Practice some basic Spanish before you arrive. This isn’t Europe – a lot of people do not speak English. I did some Duolingo before I came, and wrote down some phrases. I also downloaded Google Translate offline, for when I was in a slight pickle.
- Money. The money situation in Cuba is complicated, and they country had a dual currency system up to 2021. Now, the official currency in the Cuban Peso (CUP). Before you go, take out either American dollars or euros, and exchange them at the airport. However, it’s also advisable to keep some dollars or euros with you, as a lot of places will accept them (although you will be paying slightly more). Some of the hotels/homestays will also exchange money for you, which is a safe option.
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